1. Field of the Invention
This invention relates to the addition of perfluoroalkyl iodides to allyl glycidyl ether to produce perfluoro compounds which contain the reactive epoxide ring which is then capable of reacting with active-hydrogen-containing-compounds. More particularly, the active hydrogen compounds include alcohols, carboxylic acids, phenols, mercaptans, mercaptoalcohols, thiourea, hydrogen sulfide and water.
These derivatives possess marked surface active properties making them suitable for use as oil and soil repellants, as stable fluids, as sealing agents, and other purposes advantageously using a mixed fluorocarbon and hydrocarbon such as plastic coating, and in textiles, rubbers, automotive waxes, furniture polishes, and personal care products.
2. Description of the Prior Art
The presently available perfluoroepoxy compounds as disclosed in U.S. Pat. No. 3,145,222 are relatively slow to react with the active hydrogen compounds thereby making the production of derivatives expensive and/or time consuming. However, by having an allyloxy, allylether, iodopropyloxy, or iodopropylether group between the perfluoro and the epoxide groups the reactivity is much greater. Additionally, the resultant corresponding derivative exhibits much improved solubility in both water and organic solvents.
Previous reactions of fluoroalkyl iodides with organic compounds have centered about the addition of polyfluoroalkyl methyl or ethyl iodides, i.e. R.sub.f CH.sub.2 I or R.sub.f CH.sub.2 CH.sub.2 I, to low molecular weight aliphatic compounds to yield products wherein the iodide is on a carbon atom separated from the perfluoro group by more than one intervening carbon atoms. These previous compounds are thereby activated for dehydrohalogenation under the action of mild bases. Examples of these reactions are illustrated in the articles by Henne et al., J. Am. Chem. Soc. 73, 1791 (1951); by Haszeldine, J. Chem. Soc., London, 1199 (1953); as well as in U.S. Pat. Nos. 2,972,638; 3,016,406; and 3,408,411.
Other prior work dealt with reactions of polyfluoroalkyl iodides which would not occur by ultraviolet light initiation. Cf. U.S. Pat. No. 3,145,222. The reactions of this invention to from the basic adduct, which then is reacted to produce the derivatives herein, can proceed under ultraviolet light thereby differing from the above.